Stepping Out of My Style Comfort Zone

I have always loved fashion and admired those who could pull off trends easily, but I tend to play it safe (I am also one to shy away from anything trendy at first — skinny jeans, ballet flats, etc). I used to play with colour when I was younger, but have since come to the conclusion that it’s not a bad thing that I consider denim a neutral (and to be honest, dressing up on a weekday) and my wardrobe consists of mainly navy, black and grey. However, despite the fact that I am happy to have settled into my personal style in my late 20s, I still have a desire to get out of my comfort zone occasionally. Sometimes it doesn’t work (I’m still not convinced that lace-up flats will work for me, but I’ll keep trying) and other times, I end up finding something that I love completely — like this gingham bell sleeve top.

I recently ordered this top from Simons (you can also find similar styles here, here and here) and am completely in love. I love the slightly cropped length (it hits the waist of my jeans when I wear mid/high-rise denim), which is great for tucking into my favourite black skirt, the sleeves make a statement but not so much that they steal the show and the gingham pattern is all I needed to feel like this top was right in my style wheelhouse.

Do you have a style comfort zone? What do you do to step out of it occasionally?